Polyarylamine dyestuff and process of producing the same



Patented Sept. 11, 1928.

entree .srnreis PATENT when KARL 'lI-IIESS, BERNHAIRD DEICKE, AND ROBERT SCHMIDLIN, Q13 I-I6CI-I$T-ON-THE- MAIN, GERMANY, ASSIGNOR-S T0 GEASSELLI DYESTUFF COB-PURATION, OF .NEW YORK, N. Y., A CORPORATION OF DELAW'ARE. I I

POLYARYLAMINE DYEST'UFF AND FBOCESS Q33 PRODUCING THE SAME.

No Drawing. Application filed may 10, weasel-m1 No 108,111, at in Germany May 22, 1925.

" and in presence of an acid-binding,agent; the

reaction gives Very good yields. in order to accelerate the reaction there may, as usual in the case of reactions Where halogen is eX- changed, be added a catalyst. (tor instance a copper compound) or a small quantity of an organic solvent, such as alcohol. The. application of pressure may in mostcases be dispensed With.

amin-EZ-sulfonic acid, the resulting dyes-tuft The following" examples serve to illustrate our invention Without restricting our inven tron thereto.

l. 23.! parts of 1.S-diclilorotfi-dinitro- The parts are by Weight.

ride. lhe dyestuft' thus obtained dyes Wool from a i n'tly acid bath very intenseyellow tints oit good tastness to fulling and light. 'lhedyestutt has the tollowmg formula:

dyes animall'ibres a brown-yellow tint of good fastness to light and fulling.

T his dyestuti" may be represented by the following graphical formula:

o n (I n O 7 1103s Nn NH SOxH 3. It the operations according to Example 1 are carried out by using 56 parts or" 4:- methyl-e-aminodiphenylamin-Q-sulfonie acid instead of t -nitro-t-aminodiphenylamin- Q Nn O Morn N02 on; Hois \NH NH 2sul'tonic acid, a dyestutt is obtained. which dyes Wool brilliant orange-yellow tints. The dyestufi corresponds to cal "formula:

the following graphi- 4. 25.1 parts of 2.6-dichloro-3.5-dinitrotoluene are combined with 500 parts of water, in which 30 parts of calcined sodium carbonate have been dissolved, and 52.8 parts of 4-aminodiphenylamin-2-sulfonic acid. After addition of part of copper sulfate the whole is boiled for hours. The resulting deep reddish-brown solution is filtered and the coloring matter is salted out. The dyestuff-dycs wool a brown tint of good fastness X X NO wherein atlcast one symmetrical X-Y pair represents sulfonic acid groups, the other symmetrical X'-Ypairs represent hydrogen of a 4-aminodiphenylaminsulfonic acid com- X NO:

wherein at least one symmetrical X-Ypa-ir represents sulfonic acid groups, the other symmetrical XY pairs represent hydrogen or a monovalent substit-uent and Z represents hydrogen or methyl. 7

8. Material dyedjwith a dyestufl' of claim 7.

Y NH w jl L Y to light and fulling. It ma by the following graphical fbrmula:

UNHD N01 NOg/(INHU HOxS N11 \N13; scan The new dyestuffs of the present invention may be represented by the general formula:

3. Process of producing dyestuffs, which consists in condensing a 1.3-d1 halogen-4.6-d1- mtrobenzene compound Wlth. two molecules of a fl-amino-l-diphenylamin-2-sulfonic acid compound. 7 i

4. Process of producing dyestuifs, which consists in condensing a 1.3-dichloro-4.6-din itrobenzen, compound with two molecules of a 4-21mino-1-diphenylamin-Q-sulfonic acid compound.

5. As a new product, the dyestufi of the following composition NH NOUNOUNHO 110, N11 m1 80:11

be represented 6. Material dyed with the dyestuf f defined in claim f). t

7.'A.s new products, dyestuffs of the general formula: i

In testimony whereof, We aflix our signatures.

KARL THI ES S. BERNHARD DEIGKE. ROBERT SGHMIDLINL 

